How to Plan a Trip: Practical Travel Planning Tips

A comprehensive travel planning guide. Learn how to plan a trip from scratch, with plenty of travel planning resources to help you vacation stress-free!

I love travel. It’s in my blood: my grandmother is over 90 and has, for as long as I can remember, been in a near-constant state of exploring this planet. So I was born with the travel bug, as I’m sure many of you reading this were too. And because I love to travel, I also love talking about travel. Hearing other people’s stories and experiences fuels my own excitement and passion for travel. I have found, through these many conversations with similarly wanderlust-afflicted friends, that everyone’s travel style is as unique and different as their personalities. For my husband and I, the best vacations are planned in advance, and that’s the style that works best for us. Of course, when I say we plan travel in advance, I don’t mean that we schedule out a travel itinerary minute-by-minute: that’s too stressful! (And frankly, too much work for us. Are we lazy or efficient? You decide.) But we also make sure not to plan too little : showing up for a trip and not knowing where to go or what to do is far too nerve wracking for us! Striking a balance between those two extremes, Goldilocks style, is what works best for us. After years of travelling together, we’ve learned how to plan a vacation that works for us, without too much left open-ended or pre-scheduled.

Travel planning tips you’ll find in this post

Fair warning: this is a very long and in-depth post! You might want to bookmark it now to reference it again later. Here’s what’s included in this super comprehensive post to help you learn how to plan a trip.
Estimated Reading Time: 25 minutes

If this sounds like travel planning takes some effort, you’re not wrong. But it’s SO worth it to reduce stress while you’re travelling! And for us, the planning and research process actually makes us MORE excited for our trip. Researching all the exciting things we’re going to be doing on our trip just enhances our anticipation, and preparing for the worst eases our anxiety. So I promise, this will all be worth it. Ok, good pep talk. Ready to dive in?

The gothic quarter in Barcelona, Spain.
We always try to take cute travel photos and it never works out quite right. Anyway, this is in Barcelona, Spain.

How to Plan a Vacation: What NOT to Plan

It’s important to balance out planning for a trip so that your days don’t feel overly stuffed. I firmly believe that each minute spent wasted in the hotel looking stuff up is a minute I’m not getting to enjoy my trip! But in the same vein, if we map out every single day of my trip down to each tiny detail, we get stressed when our travel plans inevitably fall apart and our entire perfectly planned day – or week, or month – is ruined. As the sort of travelers who are prone to accidents and seem to attract catastrophes and travel fails, we’ve learned that always expect the worst. A well planned trip requires room for failure and flexibility. Here’s what I recommend not worrying about when you plan a trip!

  • When planning a trip, don’t plan out every single day. Planning each day of your vacation can set you up for disappointment: maybe one day you wake up not feeling up for the activities you have planned, perhaps the weather turns, maybe you find something else you’d like to do instead once you arrive. Sometimes it’s unavoidable, but whenever you can help it, allow yourself room for change.
    • Instead, plan out a few day options to choose from: perhaps a group of activities all in one area, or a day of seeing museums, etc. Each day, you can choose from your options depending on what you feel like doing that day! Also, allow yourself at least a day or two each week that is totally unplanned: that way, you can go back and do whatever you might have missed, explore somewhere new, or just take a day off from exploring to relax!
  • When planning a trip, don’t plan out every meal.   Your hunger levels may be unpredictable when you travel (we find ourselves getting hungrier, thanks to our increased activity levels) and holding out for the perfect meal could end up in hanger and frustration.
    • Instead, pick one or two restaurants that you would be willing to go out of your way for, or maybe write down a few options. But don’t plan on going to all of them, and definitely don’t plan out which ones you’ll go to when! Leaving your meals totally unplanned is OK too: you can find some fantastic options by asking locals or other travelers you meet for recommendations. Looking for a spot filled with locals is a safe bet, too.
  • When packing for a trip, don’t plan out every outfit. Packing individual outfits adds up quickly and can easily make your reasonable carry-on bag escalate to an expensive checked bag. Besides, everything from the weather to your mood each day could change, and your pre-planned outfits may no longer be useful.
    • Instead, pack clothes that all go together and can be mixed and matched easily. I like to keep all the clothes I bring in the same family of colors, with a few basic templates: pants + shirt + cardigan + scarf, say, and then I bring 2 pairs of pants and 4 shirts and 2 scarves to mix and match.
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Exploring the gorgeous old stepped roofs of Brugges, Belgium.
Exploring the gorgeous old stepped roofs of Brugges, Belgium.

Now that you know what you don’t need to worry about, what steps should you when planning for a trip? Here are each of the steps we take when we plan travel, and all of the resources we use! You can use this as your guideline for how to plan a trip. And guess what? We think part of the fun of travelling is planning a trip!

How to Find a Travel Destination

Sometimes you know you want to go somewhere, but don’t yet know exactly where. This is step 1 of how to plan a trip! Browsing for travel destinations  with an open mind can be really fun (and a little addictive)! Here’s how we figure out where to go when we plan travel.

  • We scour pictures on reddit or Pinterest for destinations that look incredible, and then google that location for more information.
  •  We shop on AirBnB like we’re browsing for clothes, making wishlists of places to visit. Once we find an amazing AirBnB, we’ll Google the town it’s in. We’ve planned a lot of trips to places we’d never heard of before using this method!
  • We search on Googe Flights, which can show you the cost of flying everywhere in the world from your home town on the dates you specify. We’ve scored some great deals on places we might not have otherwise visited!
Basilica del Voto Nacional in Quito, Ecuador
One thing to do in Quito, Ecuador? Visiting the awesome Basilica del Voto Nacional in the Centro Historico. Research done.

Planning What to Do & Where to Go

This is always the most fun part of planning for a trip: finding all the super fun things we’ll do once we arrive! We compile a list of things we’re interested in for our destination: a few museums, a couple of cool neighborhoods to explore, a few food recommendations, some walking tours, that sort of thing. We try to utilize advice from travelers who have been there before. But how do you find fun activities to do when planning for a trip?

  • You can always Google “best things to do in [insert destination]” but that can take a lot of time to sift through. A better option? Pinterest! Pinterest is my favorite visual search engine and it’s full of fantastic travel articles and travel tips. Just search for your destination and you’ll find loads of travel articles that will help you plan your trip!
  • WikiVoyage is super helpful for planning for a trip. It’s basically like Wikipedia, but for travel! Compiled by travelers and frequently updated, you’ll find everything from where to go and what to do, to how to get around and other useful information.
  • I like using the /r/travel subreddit or Trip Advisor to pull suggestions. Again, search for your destination and see what comes up from other travelers.
  • Once we’ve got plenty of options, we start to compile a list of all the places we’ve found in a document that we can pull up easily on a phone or Kindle when we’re travelling. At first, this list is usually enormous, but eventually we go through again and remove everything that’s repetitive or doesn’t sound as good anymore.  Remember this for later, because this document is going to come up again!
Tito the Llama at Llullu Llama hostel in Insinlivi on the Quilotoa Loop in Ecuador.
One plus to staying in hostels? Hostel pets! Tito is the resident llama at Llullu Llama on the Quilotoa Loop in Ecuador. Beat that, Marriott.

How to Plan Vacation Accommodation

After we figure out where we want to visit and have started to get an idea of what we want to do there, our next step when we’re planning a trip is booking our accommodation. At this point, we typically have some idea of where the stuff we want to focus on is – the cool neighborhoods, that kind of thing – and we can search for accommodation nearby what we want to do. We always prefer to book sleeping arrangements in advance: showing up and figuring it out is something we have tried and found that we really didn’t enjoy! If that’s your preferred method, feel free to skip this step. Here’s how we find our accommodations when planning a trip.

  • We like using HostelWorld to find budget-friendly hostels, hotels, and bed & breakfasts in our destination. Hostelworld is our preferred site for booking hostels, but we also always use TripAdvisor to see if a place has more reviews or photos before we book it.
  •  We often prefer to stay in an AirBnB rather than a hotel. In an AirBnB, the amenities are usually better, they’re almost always cheaper, and the location of someone’s house is typically much more accessible than a hotel, which is usually built on the outskirts of a city. We always check AirBnB to see what our options are for accommodation!
  • If we have credit card points and our travels include a city, we’ll see if we can book a hotel there using our credit card points. Hotels are sometimes on the outskirts of town, which makes visiting the city center expensive and time-consuming. Look for a hotel as close to the city center or public transit as possible.
  • If we do need to book a hotel and can’t use credit card points, we prefer to avoid chain hotels such as Marriott or Best Western. Why? We like to support local businesses, and we enjoy the local flair of a smaller, independent hotel or bed and breakfast. The owners are usually full of helpful suggestions for things to see and do, and it makes our trip feel more special and one-of-a-kind than it would if we were visiting the same hotel in each new place. This is totally personal preference, but it’s what we like best! To find a great local hotel or bed & breakfast, use Google or search on Pinterest.
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Eco Hostel Yuluka is just outside of Parque Tayrona on Colombia's Caribbean coast. It's one of the best hostels in Colombia!
Planning our arrival for this hostel included knowing the specific city block to find a bus to catch to a specific mile marker in the middle of freaking nowhere, Colombia. I’m so glad we wrote it down!

How to Plan your Arrival

I want my first moments in a destination to be as low-stress as possible. I don’t want to step off a long plane ride, bleary and tired, in a new place with loads of exciting and confusing new things, and then have to puzzle out how to get to my hotel safely and without getting scammed. Especially when arriving somewhere that isn’t primarily English speaking, it’s so easy to get confused and lost, which ruins your first impression and first moments in a new place! Pre planning your arrival when you plan travel is a huge step to reducing misery and stress.
  • Once we know where we’re sleeping (which is always the first place we’ll go) we plan out how we’re going to get to the hotel/hostel/AirBnB and record this information somewhere that we can access offline, like written down in a notebook or on a document saved to your phone. Remember the document I mentioned earlier? This will be the master document we end up using for everything!
  • Things to figure out in advance: Is a cab the cheapest option? Or do cabs at the airport take advantage of tourists and upcharge them like crazy? Can I get a cheaper fare by walking down the street and hailing a taxi? Is my hotel right off a local bus or train line? Is there Wi-fi in the airport? How much should a taxi cost?
  • We write down (or have on our phones) the name & address of my hostel/hotel, clearly visible and readable. This way we can show it to someone we’re having difficulty communicating with. This is helpful for asking someone at the airport or bus station how much it should cost to get there or what the best way to get there is (in case information wasn’t available online) and especially for communicating with taxi drivers. Plus it’s insurance just in case you get lost and forget where you need to go!
  • In our document, we always include walking, driving, or transit directions to the hotel so that in case there’s no Wi-Fi or data while we’re in transit, we can still find where we’re going. We’ve had to walk a taxi driver through getting us to our destination many times, so this is really a lifesaver in a pinch. You can write down instructions in your notebook or offline document,  or use Google Maps. You can create an an itinerary using Google Maps and safe it for offline use. Just follow this step by step tutorial: How To Export Your Google Map Itinerary To Your Phone & Use It Offline!
This is my pride and joy: our massive travel planning document for our backpacking trip to South America! We made it on OneNote and then downloaded it to a PDF that was stored on our phones for reference.
This is my pride and joy: our massive travel planning document for our backpacking trip to South America! We made it on OneNote and then downloaded it to a PDF that was stored on our phones for reference.

Planning Travel Logistics

By now, we have a document started with our accommodation information & how to get there, plus a bunch of stuff we’re interested in doing when we arrive. So at this point, we spend time researching logistics for all of those places and things to do in our destination.  What we’ll do is compile everything into a nice PDF or shared Google document that we can each pull up on our phone or Kindle. I prefer using OneNote to create that file and export it as a PDF, but Jeremy prefers to use a Google Doc. This document will becomes our bible while we’re travelling! Here’s what we add to our travel document for each point of interest or attraction we’ve found while researching and planning for a trip.

  • How do I get there/what transit do I take?
  • How much does it cost?
  • What are the hours it’s open?
  • What travel tips have I found online for this attraction?

Once we’ve got all of the logistics taken care of, we won’t have to spend any time sitting in our hotel room frantically Googling our plan for the day, or or worse, wasting our time to get somewhere only to find out it’s closed or too expensive. Instead, we simply wake up, scroll through our document and find whatever we feel like doing that day, and have all of the information we need already available.

The colorful streets of the Candelaria district in Bogota, Colombia are also a hotbed of theft and can be dangerous after dark! Follow these basic travel safety tips to prevent theft while traveling.
The colorful streets of the Candelaria district in Bogota, Colombia are also a hotbed of theft and can be dangerous after dark! When planning a trip, be sure to research things that will help you avoid theft and minimize risk.

How to Minimize Risks While Traveling

We love travel, but we don’t like dangerous travel. There are several steps we take to minimize risk on our travels. Read more about our favorite basic travel safety tips here.

  •  If travelling abroad, we research vaccines or medications we will need using the CDC website . We also visit a travel clinic or doctor well before we leave to get all of our health needs taken care of in advance. Note: for our non-American readers, your process for getting vaccines may be somewhat different. For example, here’s a helpful resource on travel vaccinations in Ireland.
  • We look up what documentation we will need for each country: proof of vaccines, Visa requirements, etcLonelyPlanet has a “survival guide” that covers all this information for each country.
  • We research the likelihood of theft or what neighborhoods to avoid, and common ways that travelers get taken advantage of in each location, by sifting through advice from travelers leaving comments online.
  • We stay up to date on political tensions and unrest. We avoid areas that are unsafe and situations that could compromise our safety as much as we can.
  •  We keep others up to date on our travel plans. Before we take off on a long trip, we make sure someone close to us has an itinerary so that they know where to find us and when they can expect to hear from us. It eases both our mind and theirs.
  • We purchase Traveler’s Insurance so that we’re covered in the case of emergencies. Our favorite Travel Insurance provider is World Nomads!
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A sample budget for Colombia, South America trip planning.
Here’s a sample of our budget from Colombia while planning a trip to South America! We compile everything on an excel sheet that we update frequently right up until our trip.

How to Save Money for Travel

Now that our planning is well underway, we start to save for our trip. Really, we do this year-round, but when we have a trip coming up, we kick our budgeting into high gear! Here are our favorite ways to save money for travel.
  • While we’re planning a trip, we create a trip budget to plan and estimate our expenses. To estimate our travel budget, I use averages and estimates I find online using sites like BudgetYourTrip. Once we know how much our trip will cost, we start saving money with our vacation in mind.
  • We give up small luxuries in our everyday life to put towards travel. Every time I find myself idly browsing for clothes, or buying a coffee I could have made at home, I think “$10 buys me a night in a hostel in South America,” and cut myself off. Every dollar we don’t spend adds up … to money we’ll spend later on travel!
  • We gave up our car and instead, take public transportation or bike everywhere. We use Zipcar or rent a car for weekend road trips. This isn’t an option in most places in the USA, but if it is doable for you, we highly recommend it. The savings are huge!
  •  We maintain a monthly/yearly budget for travel so that we always have money set aside for trips. We use Mint.com  for budgeting and tracking all of our expenses.
  • We research ways to save money while travelling: the cheapest hostel, the most cost efficient method of transportation, is there a nearby grocery store and a kitchen we can use near where we’re staying, what credit card or ATM fees I might incur (talk to your bank! Avoid foreign transaction fees!), which way of visiting a tourist attraction is the best deal, etc.
  • We book whatever we can as early as possible – the longer you wait, the more prices go up. This is true of flights, cars, and hotels, and even food tours or museum tickets. Book early!
  • We save and splurge on our trip carefully. For example, a good trip for us always includes some delicious food we can only get at our destination. So we choose a few places to eat that we’re really excited about – 1 meal a day – and buy or bring groceries for the rest of my meals. This works great at a place like Disney World, where one meal in Epcot is well worth a day of protein bars and apples! Read more tips for Disney World here.
  • We use credit card points and miles to save on big expenses like airfare. We have a few travel credit cards that we use frequently to build up points: a Barclay Arrival card, a Chase Sapphire card, and a Capital One Venture card. All of these cards are foreign transaction fee free and reward us with points or miles that can be redeemed for cash or other travel benefits. They aren’t restricted to a single airline or hotel chain, which is huge since we aren’t particularly loyal. And they offer huge sign-up bonuses! If you concentrate all of your spending on these 3 cards routinely – that’s 2 people’s worth of spending, for us – you’ll get a decent amount of cash back. A huge caveat: DON’T get into credit card points and miles if you tend to carry a balance on your credit cards. It’s not worth it! 
  • We use a debit card with no ATM fees or foreign transaction fees from Charles Schwab. Cash is king in most developing nations, and we save hundreds by avoiding these annoying fees every time we withdraw cash while travelling abroad.
Wandering the streets of Brugges, Belgium.
When packing for a trip, always bring something bright that will stand out well against the backdrop of a cityscape. Just kidding, we happened to get lucky. But that’s probably good advice….

What to Pack for a Trip

We know where we’re going, we’re super stoked for all of the fun activities we’ve found to do there, and we’ve saved up money for a great trip. What’s next? Figuring out what to pack! There’s a thin line between “I packed too much and now I’m miserable schlepping my bag around” and “I didn’t pack enough and now I have to buy a bunch of expensive stuff I already have at home!” The trick is finding that balance. (We didn’t find it on our last trip – read about what NOT to pack and learn from our mistakes.) Here’s how I plan out what to pack for a trip in advance.

  • Clothes: To plan my clothes for a vacation, I think of the environments I’ll encounter on my trip. What will the weather be like? Will I be doing anything active? Will I be going anywhere fancy? Then, I try to bring items that multitask as much as possible. For example, a dress is great for warm weather, I can add a cardigan to make it fancy, or a scarf or belt for variety. I try to make things like pants multitask as much as possible – you don’t need a pair of pants to look fancy AND casual, just a different top or jacket! I lay everything out and make sure it all mixes & matches – and yes, I try to go for a ~color palette~, I do work in the fashion industry after all!
  • Toiletries: You don’t need your whole bathroom. Just bring the basics: shampoo, conditioner, soap, moisturizer, some travel makeup necessities, a nail file and clippers. And put everything in small bottles. There’s no reason your toiletries shouldn’t fit in a small ziplock or zippered bag. As for hair tools, personal preference: I usually leave mine at home, but I do have a tiny travel hair straightener  that I bring.
  • “Just In Case” Items: I’m all about being practical, so I do pack plenty of “just in case” items, but they don’t take up much space. I squeeze some sunscreen into a small bottle to take with us. A small bottle of ibuprofen. A tiny travel-friendly first aid kit and sewing kit. Condoms. You know, the necessities. If it’s big and bulky, highly unlikely that you’ll need it, and/or easily found in a pharmacy or mainstream chain store, leave it at home.
Couple overlooking Machu Picchu, Peru
We wish we’d known more about the logistics of hiking the inca Trail to Machu Picchu before we failed it miserably. Luckily, you can avoid our mistakes! Always do your research in advance when planning for a trip.

Websites & Online Travel Planning Resources

We mentioned a lot of websites  and resources above, but here they all are in one place for your convenience. And just in case you’re craving even MORE useful information (kudos to you), Travel for your Life also has a fantastic and comprehensive list of useful travel resources.

Bookmark this page to reference these travel planning resources later!

Travel Resources: Where to Go & What to Do?

  • WikiVoyagelike the name implies, WikiVoyage is Wikipedia for travel destinations. Written and maintained by travelers. Just type in your destination! There’s also an offline version of WikiVoyage in the app store, so that you can access downloaded pages for your destinations whether you have wifi or not
  • The /r/travel subreddit: Fantastic to browse for getting inspiration about where to go from trip reviews and photos, or searching for a specific location to see recommendations and advice.
  • Pinterest: Pinterest is a visual search engine that’s fantastic for browsing and compiling photos, travel tips, and itineraries. I like to create a board specifically for a single trip and add everything I find about that location to that board for my own reference.
  • TripAdvisor: The old standard for travel reviews and recommendations. This site has been around for ages, so most places have hundreds of reviews. I like to vet a place I’ve found using TripAdvisor before booking: primarily hostels/hotels, or maybe a city or tour. There are usually more user submitted pictures of a hostel on TripAdvisor than I can find on a site like HostelWorld, and more reviews. The only downside with TripAdvisor is that a lot of the travelers tend to be older and a little more risk-adverse and less cost-conscious than I am, so I read some of their reviews with that in mind.

Travel Resources: Where to Stay?

  • AirBnB: Many a weekend trip has been based off of a cool AirBnB we found and decided to book. Because AirBnB’s are personally owned and rented by regular people, the variety is endless – you can rent a beautiful house right next to Salt & Straw in downtown Portland, or an electricity free cabin with a composting toilet on a working coastal farm in Mendocino (let us know if you want the links to those!). You can find AirBnB’s in places that no hotels are allowed to operate, like neighborhoods, or where no hotels WANT to operate, like tiny towns on remote scenic highways. And they almost always have great amenities (kitchens! hiking trails! pets!) for less than the cost of a hotel room! I also love AirBnB’s for group outings – everyone gets a room, there’s a huge shared kitchen, and the more people means a lower cost. All in all, check it out if you haven’t yet.
  • HostelWorld: Our favorite site for booking hostels, bed & breakfasts, and inexpensive hotels. The reviews are usually honest and helpful, so I can make sure my hostel has A/C and hot showers as advertised, or evaluate the location. The site is clear and easy to use, booking is free (we do recommend paying the $2 security fee though, in case you need to make a change later and want to reuse your deposit), there are always clear instructions on getting to the hostel written by the owners, and I have peace of mind knowing that my bookings are stored somewhere electronically, as hand written or emailed reservations can sometimes get lost. Don’t make the mistake of assuming “hostel” means sketch, dirty, or full of young college students partying – those are certainly out there, but carefully reading reviews and looking at photos can help you find some REALLY amazing options!  We’ve stayed in some incredible hostels, such as these hostels in Colombia.
  • ReserveAmerica: My favorite site for USA campsite reservations. A little clunky to use, but once you get the hang of it, it’s fine. Campsites are released in blocks 6 months in advance, so that for really competitive campsites (lookin’ at you, Yosemite), you may actually need to hop on it ASAP once it’s available! For those of us who aren’t thinking about their June campsites on New Years, you can also set a Notification for a specific campsite and date range, and when someone cancels their trip, you’ll get an email letting you know a spot has become available. I’ve gotten some incredible spots in prime campsites that way – you just have to be OK with some potentially last minute camping weekends.

Travel Resources: Practical & Safety Information

  • The CDC Travel Site: Researching disease prevention: it’s not glamorous, but it’s safe and it’s smart. Know what to protect yourself from and how for the countries you’re visiting.
  • LonelyPlanet: I typically use LonelyPlanet only for their practical and logistic information. They call them “Survival Guides” and they contain detailed information about visas, documentation, paperwork, health advisories, transit, currency, and other really important basic information. I like to search a country and lay out all that practical information in advance.

Travel Resources: Save Money for Travel

  • BudgetYourTrip: Compiles traveler submitted data to provide average prices for various commodities with variable travelling style, so you can select how fancy you plan to get and then plan accordingly. Also has some helpful travel tips and food suggestions as a bonus!
  • Google Flights: The best search engine to find cheap flights, in my opinion. Scours the web and all kinds of airlines that aren’t often included in flight comparison sites. Also, you can search for “Everywhere” as a destination and just see what’s affordable from your home airport!

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A comprehensive travel planning guide. Learn how to plan a trip from scratch, with plenty of travel planning resources to help you vacation stress-free!

What are your favorite tips for travel planning? Did we miss anything? Leave us a comment!